Should I exercise my startup options after leaving?
How to think about exercise windows, cash at risk, AMT exposure, and private-company uncertainty.
Start with cash at risk
Exercising options usually means paying the strike cost before you know whether the shares will ever become liquid.
That cash risk is personal. A grant that is rational for one employee can be impractical for another.
Tax can arrive before liquidity
Depending on option type and jurisdiction, exercising can create tax exposure before you can sell shares. US ISO holders should pay particular attention to potential AMT.
Grantwise estimates AMT exposure separately because it is an exercise-time risk, not an exit payout.
Use scenarios to make the decision less abstract
Compare what you pay today against the realistic range of outcomes. If the downside is zero and the cash cost is meaningful, the decision deserves care.
A model will not tell you what to do, but it can show what must be true for the exercise to make sense.
Model your offer
Turn the theory into numbers.
Use the checker to model dilution, strike cost, tax, AMT exposure, and liquidation preference across four outcomes.
Open equity checker